Rhizoxin
Chemical compound
From Wikipedia, the free encyclopedia
Rhizoxin is an antimitotic agent with anti-tumor activity.[1][2] It is isolated from the fungus Rhizopus microsporus which causes rice seedling blight.
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3D model (JSmol) |
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| ChEBI | |
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PubChem CID |
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CompTox Dashboard (EPA) |
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| Properties | |
| C35H47NO9 | |
| Molar mass | 625.749 g/mol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Biosynthesis
Rhizoxin is biosynthesised by Paraburkholderia rhizoxinica, a bacterial endosymbiont of the fungus Rhizopus microsporus.[3] It is one of a large group of rhizoxin-like compounds produced by the bacteria.[4] The bacterial endosymbiont can be grown independently in culture. This may allow easy harvesting of rhizoxin and the related compounds avoiding total chemical synthesis, although total chemical synthesis is possible.[5]
Cytotoxic function
Rhizoxin binds beta tubulin in eukaryotic cells disrupting microtubule formation. This, in turn, prevents formation of the mitotic spindle inhibiting cell division. Additionally rhizoxin can depolymerise assembled microtubules.[6] The function of rhizoxin is similar to Vinca alkaloids.
Rhizoxin has undergone clinical trials as an anti-cancer drug[7] although it did not reach later stages of clinical trials due to low activity in vivo. Related compounds to rhizoxin have improved biological activity (E.G Mertansine) .[4]
Structure
Rhizoxin is a 16-membered lactone ring connected to an oxazole ring by a long unsaturated chain.[8]